He could feel powerless. If he is in a situation where he has no choice but to dress as a girl, like if it's an authority figure forcing him, he might feel like he has no control over his own appearance. This can lead to feelings of low self - worth and a sense of being violated. He may start to question his own identity and where he fits in society's gender expectations.
He probably feels embarrassed. Dressing in a way that goes against his gender identity in public or even in private can be mortifying.
At first, he could be angry. After all, his autonomy is being taken away. But as time passes, he may start to have mixed feelings. He could find some aspects of the girl's clothing comfortable or interesting, while still being resentful of the situation. He might also start to empathize more with girls if he experiences some of the things they do while dressed as one, like the way people interact with him differently or the types of comments he gets.
He may initially feel a sense of shock. It's unexpected to be forced into such a situation. And as time goes on, if he can't escape this forced dressing, he could feel a deep sense of helplessness. He might be constantly worried about what others will think of him and may start to withdraw from social interactions out of fear of being ridiculed.
He might feel embarrassed. Dressing as a girl goes against the traditional gender norms he is used to, and he may be worried about what others will think of him. He could also feel angry that his will is being violated and he is being forced into something he doesn't want to do.
In some cases, the boy could feel angry or resentful. If it was forced upon him against his will, he may see it as an infringement of his identity. He might struggle with the idea of conforming to something that he doesn't identify with, and this could lead to conflict within the story, either with the people who made him do it or with his own self - perception.
He could be confused as well. If he doesn't understand why he has to wear the dress, especially if there is no clear explanation given, he might be left in a state of confusion about the whole situation and wonder what he did wrong to be put in such a position.
He could be feeling a whole range of negative emotions. First of all, there's the obvious discomfort. Dresses are not something boys typically wear, so physically it might be uncomfortable. Emotionally, he might be in a state of shock, especially if it was sudden. Then comes the sense of powerlessness, as he has no choice in the matter. He may also feel betrayed if it was someone he trusted who forced him, like a friend or family member. This could lead to long - term trust issues. And on top of all that, he might be worried about the long - term consequences, like being teased or bullied further in the future because of this incident.
He may feel a bit self - conscious at first. Wearing girl's clothes is not the norm for him. However, if his sister is positive and supportive during the process, he could gradually feel more at ease. He might also feel a sense of creativity being unleashed as he participates in this unique activity. And depending on the reactions he gets from others (if any), he could either feel more confident or a bit shy about his new appearance.
He would probably feel embarrassed. Wearing something that goes against the traditional gender - associated clothing for boys in a forced situation is likely to make him feel self - conscious in front of others.
He could feel angry. It's his body and his hair, and being forced to have it styled in a way he doesn't like is a violation of his autonomy. He may also feel frustrated if he tries to resist but is still made to go through with it. Imagine trying to say no but no one listens. He'll be seething inside.
He might initially be very resistant. He could protest and try to avoid it at all costs, feeling embarrassed and self - conscious about wearing girl's clothes.